FENOPROFEN CALCIUM ANHYDROUS

Details

Stereochemistry	RACEMIC
Molecular Formula	2C15H13O3.Ca
Molecular Weight	522.602
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of FENOPROFEN CALCIUM ANHYDROUS

Structure Search

SMILES

[Ca++].CC(C([O-])=O)C1=CC(OC2=CC=CC=C2)=CC=C1.CC(C([O-])=O)C3=CC(OC4=CC=CC=C4)=CC=C3

InChI

InChIKey=VHUXSAWXWSTUOD-UHFFFAOYSA-L

InChI=1S/2C15H14O3.Ca/c2*1-11(15(16)17)12-6-5-9-14(10-12)18-13-7-3-2-4-8-13;/h2*2-11H,1H3,(H,16,17);/q;;+2/p-2

HIDE SMILES / InChI

Molecular Formula	C15H13O3
Molecular Weight	241.2619
Charge	-1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	Ca
Molecular Weight	40.078
Charge	2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00573
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/fenoprofen.html

Fenoprofen is a propionic acid derivative with analgesic, antiinflammatory and antipyretic properties. Fenoprofen inhibits prostaglandin synthesis by decreasing the enzyme needed for biosynthesis. In patients with rheumatoid arthritis, the anti-inflammatory action of fenoprofen has been evidenced by relief of pain, increase in grip strength, and reductions in joint swelling, duration of morning stiffness, and disease activity (as assessed by both the investigator and the patient). In patients with osteoarthritis, the anti-inflammatory and analgesic effects of fenoprofen have been demonstrated by reduction in tenderness as a response to pressure and reductions in night pain, stiffness, swelling, and overall disease activity (as assessed by both the patient and the investigator). These effects have also been demonstrated by relief of pain with motion and at rest and increased range of motion in involved joints. In patients with rheumatoid arthritis and osteoarthritis, clinical studies have shown fenoprofen to be comparable to aspirin in controlling the aforementioned measures of disease activity, but mild gastrointestinal reactions (nausea, dyspepsia) and tinnitus occurred less frequently in patients treated with fenoprofen than in aspirin-treated patients. It is not known whether fenoprofen causes less peptic ulceration than does aspirin. In patients with pain, the analgesic action of fenoprofen has produced a reduction in pain intensity, an increase in pain relief, improvement in total analgesia scores, and a sustained analgesic effect. Indicated for relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Also for the relief of mild to moderate pain.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00573	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Pain 619 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Palliative	Approved 8583	NALFON Approved Use NALFON is a nonsteroidal anti-inflammatory drug indicated for: • Relief of mild to moderate pain in adults. • Relief of the signs and symptoms of rheumatoid arthritis. • Relief of the signs and symptoms of osteoarthritis. Launch Date 1976
Rheumatoid arthritis 320 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Primary	Approved 8583	NALFON Approved Use NALFON is a nonsteroidal anti-inflammatory drug indicated for: • Relief of mild to moderate pain in adults. • Relief of the signs and symptoms of rheumatoid arthritis. • Relief of the signs and symptoms of osteoarthritis. Launch Date 1976
Osteoarthritis 157 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Primary	Approved 8583	NALFON Approved Use NALFON is a nonsteroidal anti-inflammatory drug indicated for: • Relief of mild to moderate pain in adults. • Relief of the signs and symptoms of rheumatoid arthritis. • Relief of the signs and symptoms of osteoarthritis. Launch Date 1976

C_max

Value	Dose	Co-administered	Analyte	Population
28.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
105.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
400 mg 3 times / day steady, oral Recommended Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Disc. AE: Reaction gastrointestinal, Reaction skin... Other AEs: Dyspepsia, Nausea... AEs leading to discontinuation/dose reduction: Reaction gastrointestinal (2%) Reaction skin (1%) Cardiovascular disorder (NOS) (0.5%) Other AEs: Dyspepsia (10%) Nausea (7.7%) Constipation (7%) Vomiting (2.6%) Abdominal pain (2%) Diarrhea (1.8%) Headache (8.7%) Somnolence (8.5%) Dizziness (6.5%) Tremor (2.2%) Confusion (1.4%) Sweating increased (4.6%) Pruritus (4.2%) Rash (3.7%) Tinnitus (4.5%) Blurred vision (2.2%) Hearing decreased (1.6%) Palpitations (2.5%) Nervousness (5.7%) Asthenia (5.4%) Peripheral edema (5%) Dyspnea (2.8%) Fatigue (1.7%) Upper respiratory infection (1.5%) Nasopharyngitis (1.2%) Gastritis (<1%) Ulcer peptic with perforation (<1%) Ulcer peptic with perforation (<1%) Gastrointestinal hemorrhage (<1%) Anorexia (<1%) Flatulence (<1%) Dry mouth (<1%) Blood in stool (<1%) Alkaline phosphatase increased (<1%) LDH increased (<1%) SGOT increased (<1%) Jaundice (<1%) Cholestatic hepatitis (<1%) Buccal mucosa aphthous ulceration (<1%) Taste metallic (<1%) Pancreatitis (<1%) Atrial fibrillation (<1%) Pulmonary edema (<1%) Electrocardiogram change (<1%) Supraventricular tachycardia (<1%) Renal failure (<1%) Dysuria (<1%) Cystitis (<1%) Hematuria (<1%) Oliguria (<1%) Azotemia (<1%) Anuria (<1%) Nephritis interstitial (<1%) Nephrosis (<1%) Acute papillary necrosis (<1%) Angioedema (<1%) Purpura (<1%) Bruising (<1%) Hemorrhage (<1%) Thrombocytopenia (<1%) Hemolytic anemia (<1%) Aplastic anemia (<1%) Agranulocytosis (<1%) Pancytopenia (<1%) Depression (<1%) Disorientation (<1%) Seizures (<1%) Trigeminal neuralgia (<1%) Burning tongue (<1%) Diplopia (<1%) Optic neuritis (<1%) Exfoliative dermatitis (<1%) Toxic epidermal necrolysis (<1%) Stevens-Johnson syndrome (<1%) Alopecia (<1%) Anaphylaxis (<1%) Urticaria (<1%) Malaise (<1%) Insomnia (<1%) Tachycardia (<1%) Personality change (<1%) Lymphadenopathy (<1%) Mastodynia (<1%) Fever (<1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A1 246 UGT1A3 89 UGT1A4 98 UGT1A6 136 UGT1A9 148 UGT2B7 197	CYP1A2 1197 CYP2C8 810 CYP2E1 729 UGT2B7 456

Drug as perpetrator

Target	Modality	Activity
UGT1A1 303	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A3 99	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A4 100	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A6 171	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A9 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	yes
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23362865/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5004	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5004
ChemicalBook	CB3290884	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3290884
eMolecules	901876	https://www.emolecules.com/cgi-bin/more?vid=901876
MolPort	MolPort-003-666-345	https://www.molport.com/shop/molecule-link/MolPort-003-666-345

PubMed

Title	Date	PubMed
Letter: Aspirin sensitivity: other drugs.	1975 Feb	1115460
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation.	2001 May-Jun	11386636
[Chiral separation by capillary electrochromatography on stationary phase adsorbed with protein].	2001 Sep	12545430
Distribution of acidic and neutral drugs in surface waters near sewage treatment plants in the lower Great Lakes, Canada.	2003 Dec	14713027
Hyaluronidase inhibitors (sodium cromoglycate and sodium auro-thiomalate) reduce the local tissue damage and prolong the survival time of mice injected with Naja kaouthia and Calloselasma rhodostoma venoms.	2003 Nov	14602119
The aryl propionic acid R-flurbiprofen selectively induces p75NTR-dependent decreased survival of prostate tumor cells.	2007 Apr 1	17409433
A tale of switched functions: from cyclooxygenase inhibition to M-channel modulation in new diphenylamine derivatives.	2007 Dec 26	18159230
A peripatetic pediatrician's journey into pediatric rheumatology: Part II.	2007 Jun 21	17584931
Comparison of Prevention of NSAID-Induced Gastrointestinal Complications by Rebamipide and Misoprostol: A Randomized, Multicenter, Controlled Trial-STORM STUDY.	2007 Mar	18188417
Fenoprofen and ketoprofen amides as potential antitumor agents.	2007 Mar	17441909
Traditional nonsteroidal anti-inflammatory drugs and postmenopausal hormone therapy: a drug-drug interaction?	2007 May	17518513
Stereoselective disposition of fenoprofen in plasma and synovial fluid of patients with rheumatoid arthritis.	2007 May 5	17299730
Peroxisome proliferator-activated receptors in the modulation of the immune/inflammatory response in atherosclerosis.	2008	18769491
Synthesis and biological evaluation of O-methyl and O-ethyl NSAID hydroxamic acids.	2009 Oct	19772490
Aldosterone glucuronidation by human liver and kidney microsomes and recombinant UDP-glucuronosyltransferases: inhibition by NSAIDs.	2009 Sep	19740398
Occurrence and risk assessment of acidic pharmaceuticals in the Yellow River, Hai River and Liao River of north China.	2010 Jul 15	20493517
Primaquine-NSAID twin drugs: Synthesis, radical scavenging, antioxidant and Fe2+ chelating activity.	2010 Sep	21134866

Patents

Sample Use Guides

In Vivo Use Guide

400 mg to 600 mg orally 3 or 4 times a day -Maximum dose: 3200 mg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:10:10 GMT 2025` Edited by `admin` on `Mon Mar 31 18:10:10 GMT 2025`
Record UNII	8R95A3O51K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENOPROFEN CALCIUM ANHYDROUS

Common Name

English

2-(3-PHENOXYPHENYL)PROPIONIC ACID CALCIUM SALT

Preferred Name

English

CALCIUM FENOPROFEN

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, CALCIUM SALT

Common Name

English

CALCIUM FENOPROFEN ANHYDROUS

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, CALCIUM SALT (2:1)

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, CALCIUM SALT, (±)-

Common Name

English

Code System Code Type Description

CAS

1260485-60-6